6-Bromo-3-(2,4-difluoro-phenyl)-imidazo[1,2-a]pyridine → 3-(2,4-Difluoro-phenyl)-6-[2-(4-fluoro-phenyl)-2H-pyrazol-3-yl]-imidazo[1,2-a]pyridine

HRID 629282Notes

Reaction equation

HRID 629282 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=3[F:18])=[CH:9][N:10]=2)[CH:7]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[C:30](B3OC(C)(C)C(C)(C)O3)=[CH:29][CH:28]=[N:27]2)=[CH:22][CH:21]=1>>[F:18][C:12]1[CH:13]=[C:14]([F:17])[CH:15]=[CH:16][C:11]=1[C:8]1[N:6]2[CH:7]=[C:2]([C:30]3[N:26]([C:23]4[CH:24]=[CH:25][C:20]([F:19])=[CH:21][CH:22]=4)[N:27]=[CH:28][CH:29]=3)[CH:3]=[CH:4][C:5]2=[N:10][CH:9]=1

Participants

3

Reactant 2

HCID 901893056-Bromo-3-(2,4-difluoro-phenyl)-imidazo[1,2-a]pyridine2×HCID 901893681-(4-fluorophenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole2×

Product 1

HCID 760724923-(2,4-Difluoro-phenyl)-6-[2-(4-fluoro-phenyl)-2H-pyrazol-3-yl]-imidazo[1,2-a]pyridine

Procedure

The title compound, white solid (56 mg, 44%), MS (ISP) m/z=391.5 [(M+H)+], mp 168° C., was prepared in accordance with the general method of example 1 from 6-bromo-3-(2,4-difluoro-phenyl)-imidazo[1,2-a]pyridine (intermediate K) (0.1 g, 0.324 mmol) and 1-(4-fluoro-phenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (intermediate A) (0.11 mg, 0.38 mmol).

Sources & evidence

ORD record
ord-9cb4201292714b84b397ed91eeda7b55
Source dataset
uspto-grants-2016_04
Patent number
US09315502B2

Reaction notes

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